I Lost My Virginity to the Shyest Friend in the Group

Before I begin, I want to make it clear that everything I’m going to tell you is real. There’s nothing made up in this story, not a single detail. I decided to write it because recently I started thinking about that afternoon again and realized that, after all these years, it’s still one of the few things I remember with absolute affection.

Before I turned nineteen, I’d never had sex with anyone. I had kissed boys and girls at parties, yes—awkward, curious kisses that ended in laughter and uncomfortable silences the next morning. I suppose it was part of the way I was discovering myself. Today I can calmly say that I’m bisexual, but back then I still didn’t put a name to anything.

I’d always been very shy, and at that time I was even more so. I had very few close friends, and only one who was my age. His name was Andrés, and we’d known each other since our last year of high school. We shared the same records, the same weird movies, and an equally difficult habit to overcome: neither of us knew how to look another person in the eyes for more than three seconds. He told me about the girls he liked, and I listened without feeling anything. He was my friend, period.

One summer afternoon he called to invite me out. I accepted without thinking too much about it. It was Thursday, and the heat was heavy, the kind that clings to the nape of your neck and leaves you half-asleep. We went to the big square in the neighborhood, the one with enormous trees and green-painted benches that were almost invisible among the roots. We sat there and talked for hours about silly things, about the university we were about to start, about how we imagined ourselves at thirty. I laughed a lot—I remember that. I laughed with him in a different way from how I laughed with everyone else.

When it was beginning to get dark and we said it was time to go back, Andrés kept looking at me longer than usual. He told me, almost inaudibly, that he’d been having feelings for me for a while. I didn’t know what to say. A flush rose from my neck to my ears; my face felt like it was burning, and I imagine I was as red as a tomato. Seeing my expression, he asked me not to answer him then, to think about it calmly and tell him when I was ready. I nodded because it was the only thing my body allowed me to do.

I walked home slowly. His words kept echoing in my head. It was strange, because until that afternoon Andrés had been nothing more than a friend, and now, all of a sudden, I couldn’t stop thinking about the way his hair moved when he talked or the way he bit the nail of his thumb.

Three or four days passed, and I decided to call him. I had no idea what to say, but I needed to hear him again to understand what was happening to me. I asked him to explain more clearly what he felt. Andrés didn’t hesitate. He told me he’d always thought I was pretty, but that over the past few months he’d realized he was in love with me. He said it just like that, without embellishment, and once again left me speechless.

I answered him honestly: his words stirred something inside me, and I still didn’t really know what that something was, but I wanted to try. We started going out as boyfriend and girlfriend the next day.

***

The first two months were sweaty hands and long kisses on park benches. I avoided sex. Every time he came a little closer, I told him I still didn’t feel ready, and he respected me without complaining. Andrés had already been with two girls and knew the procedure, so to speak. I, on the other hand, was turning nineteen without ever having been with anyone.

One night in March, when summer was beginning to ease off, we went to his house to watch a movie. His parents had gone to the coast for the weekend, and the house was quiet. We put on one of those French films neither of us ever quite understood, and twenty minutes later we weren’t watching the screen anymore.

His hand began wandering over my thigh. It rose until it almost touched my hip, then moved back down slowly to just above my knee. He did it patiently, almost as if he were drawing something on my skin. I let him. We kissed with our tongues in each other’s mouths, biting each other’s lips, and I felt my whole body growing heavy, a kind of warm heaviness I’d never experienced before. My panties were beginning to stick between my legs from how wet I was getting, and I squeezed my thighs together to hide it, even though he had already noticed.

At one point he slipped his hand beneath my shirt and squeezed my tits over my bra. He pinched my nipples through the lace, and a short moan escaped me that even I didn’t know where it had come from. Then he pulled down the cups of my bra and licked my nipples one at a time, first with the flat of his tongue and then with the tip, circling them until they grew hard as two stones. Meanwhile, I kept thinking that this was it, that it was time, that there was no point putting it off if what I felt with him was exactly what I was supposed to feel. Andrés pulled away a little, his mouth still glistening, and asked me in my ear if I was ready to fuck. I told him yes. I said it softly, almost swallowing the word, but I said it.

We went upstairs to his room. It was a small bedroom with a large poster of a band I no longer remember and a yellow lamp on the bedside table. We lay down on the bed and kept kissing for a while longer, with our clothes no longer entirely in the way: he had taken off his shirt on the stairs, and my skirt was pulled up to my waist. He took my hand and guided it to his crotch. Through his pants, I felt his erect cock for the first time, thick and outlined against the denim as if it were about to burst through his fly. It was a new texture, hard and hot beneath the fabric, and it gave me a pleasant dizziness that went straight down to my cunt.

While I squeezed him through his jeans, he slipped his hand beneath my skirt and ran his fingers over my panties, pressing right against my clitoris with the pad of his thumb. I felt myself growing wetter with every caress, a thick, shameful wetness that seeped through the fabric and stained his fingers. He pushed my panties to one side and shoved two fingers inside me, all the way in. I arched my back involuntarily and let out a long gasp. He began moving them inside me, in and out, making a wet, obscene sound that filled the room. With his other hand he kept rubbing my clitoris, in slow circles at first, then faster. I clenched the sheets in my fists, biting my lip to keep from screaming. He seemed pleased, and his smile—and his fingers buried to the knuckles in my cunt—were enough to reassure me.

***

He got out of bed and began undressing. He took off his jeans and was left in his boxers. I was sitting on the edge of the mattress watching him, with a mixture of nerves and heat tightening in the pit of my stomach. His cock looked rock-hard through the fabric, almost as if it wanted to spring out on its own, and there was a damp spot right at the tip where the glans showed through. He came over to me and, a little embarrassed, asked me to suck it.

I’d never done it. I’d never had a cock that close to my face. I warned him that he probably wouldn’t like it, that I had no idea how to do it. He laughed softly and told me he didn’t care, that he just wanted to feel my mouth. I pulled down his boxers with both hands, and his cock sprang out in front of me, rigid, veins standing out along the shaft and the swollen tip shining with pre-cum. I took it carefully, as if it were something that could break, and began moving it slowly, sliding my fist up and down to watch the glans cover and uncover itself with the foreskin.

I brought my mouth closer and kissed it first, then licked it from base to tip, following one of the thick veins running along the shaft. A large drop of pre-cum had gathered at the tip, and I collected it with my tongue. It tasted salty, milder than I’d imagined. I tried to do what I’d seen in some video out of curiosity, the only reference I had. I took as much of it into my mouth as I could, pushing until the tip brushed the back of my throat and gave me a little gag, then pulling it out coated in saliva, licking the tip with my flat tongue, moving down to his balls and taking them into my mouth one at a time, sucking them carefully while I kept jerking him off with my hand slick with spit.

Andrés moaned softly, a kind of restrained whimper, and whenever the tip sank between my lips he let out a tight “fuck” through his teeth. He placed one hand on the back of my neck—not squeezing, just resting there—and began setting the pace slowly, raising and lowering my head in time with him. Hearing him gradually lose control turned me on more than anything else. I felt my cunt throbbing, so wet that I was already dripping down my thigh, and without realizing it I began squeezing my legs against my own free hand to give myself a little relief.

I was surprised by how much I enjoyed doing it. The taste, the weight, feeling it pulse in my mouth every time it reached the back of my throat. I stayed like that for quite a while, until he stopped me, breathing hard, saying that if I kept going he was going to come right away. He pulled me up by the shoulders and began taking off my clothes with hurried hands.

By then I wasn’t nervous anymore. What remained was pure horniness, an urgency that made me move differently—faster, less thoughtfully. He took off my shirt, bra, skirt, and panties, which he yanked down almost tearing them. I stood naked in front of him and, against all expectations, I wasn’t embarrassed. On the contrary, I spread my legs a little without thinking, to show him how wet I was. He stared at me for a second with his mouth open, then threw himself on top of me.

He spread my legs with both hands and buried his face between my thighs. It was the first time I’d felt a tongue there, and I thought I was going to die. He began slowly, licking me from bottom to top, gathering everything I was releasing, and then focused on my clitoris and didn’t move away from it. He sucked it, licked it in circles, took it between his lips, and gently suctioned it. I grabbed the pillow with both hands and covered my face to scream into the fabric. My hips moved on their own against his mouth. He slid his fingers inside me again while he kept sucking me, and I felt a strange tension in my belly, something building up without quite breaking. I arched, gasped loudly, and he lifted his face, completely shiny with my juices, smiling at me with swollen lips.

***

I lay back completely while he opened the condom. It took him a little while to put it on, those clumsy movements made with slightly trembling hands. I took the opportunity to touch myself, not out of arousal, but to make sure I was ready. I ran two fingers along my slit from top to bottom and pulled them out dripping. I was soaked. There was no way I could have been readier than that. I brought my fingers to my mouth and sucked them while looking at him, and he muttered “holy fuck” under his breath as he finished putting on the condom.

Andrés settled himself on top of me. My heart was beating so hard I’m sure he could hear it against his chest. He kissed me again, asked once more if I was sure, and I told him yes, to put it in me already. Then I looked down and saw him take his cock in his hand and place it at the entrance to my cunt. He began pushing slowly, rubbing the tip against my clitoris first, getting it thoroughly wet with my juices, and then searching for the opening.

It was difficult at first. Even though I was lubricated, I could feel myself opening little by little, a strange pressure unlike anything I’d felt before. He inserted the head of his glans, pulled it out, then pushed it in a little farther, advancing another centimeter each time. It didn’t hurt, but it wasn’t pleasurable at that first moment either. It was more like a new discomfort, an intrusion my body still didn’t know how to receive, a strange stretching that made me hold my breath.

After a few attempts, he pushed more decisively, and I felt him enter completely, felt his balls slap against his ass for the first time. He stayed still inside me for a moment, looking at me and letting me get used to him. Then he began to move. His balls bounced against me every time he thrust all the way in, and by then the sensation was beginning to change. I could feel his cock filling me completely, withdrawing almost to the tip and then sinking all the way back in, and with every thrust pleasure gained ground over the discomfort. There was pleasure, yes, but also some discomfort, all mixed together. We stayed like that for several minutes, him on top, moving slowly and looking me in the face as if he wanted to make sure I was all right, beads of sweat falling from his forehead onto my tits.

He grabbed my legs and lifted them onto his shoulders. In that position he went even deeper, so deep that I let out a whimper and dug my nails into his arms. He began fucking me faster, with hard thrusts, and the sound of our bodies colliding filled the room: skin against skin, the wet slapping of my cunt, the bed creaking beneath us. He watched my tits bounce with every thrust and bit his lip. “You’re so tight,” he told me in a hoarse voice, and I closed my eyes because hearing him talk like that, so crudely, filled me with a delicious embarrassment.

At some point he asked me breathlessly if I wanted to change positions. He lay on his back and told me to climb on top. I did as he asked. I sat astride him, took his cock in my hand, still hot and shining with the wet condom, and slowly lowered myself onto it. This time it slid in effortlessly, as if my cunt had already been waiting for it. I placed my hands on his chest and began to move.

I liked this position so much more. I was in control of everything: I could choose the rhythm, the depth, the angle. I experimented until I found the exact spot that gave me the most pleasure, and when I found it, I let out a longer moan that surprised even me. I moved my hips back and forth, made little jumps on top of him while feeling his cock slide in and out, and squeezed my tits with my own hands because I needed to touch my whole body. I laughed without meaning to, between moans, because I felt free for the first time in my life. Andrés looked up at me with his mouth open, squeezed my tits, pinched my nipples, and gave me light slaps on the ass that made me bounce. Every time I came down hard and buried him inside me to the base, we both moaned at the same time.

At some point Andrés closed his eyes. I felt him gripping my waist with both hands, so tightly that his fingerprints were still there afterward, and he began lifting his hips to drive himself into me from below, thrusting faster and faster. I heard a longer moan than the ones before, a tight “I’m coming, I’m coming” between his teeth, and felt his whole body shake beneath mine, felt his cock pulsing inside me as he came into the condom. I didn’t stop moving; I wanted to draw out every last drop, and he writhed beneath me, telling me to stop, that he couldn’t take any more. It made me strangely happy to make him finish like that, to feel his body surrender completely to mine, a kind of new pride I had no name for.

I lowered myself slowly, careful not to hurt him, and lay down beside him. I watched him take off the condom, full of thick white semen, and tie it in a knot before tossing it onto the floor beside the bed. Neither of us said anything for a long while. The only sounds in the room were our accelerated breathing and, in the distance, a dog barking in the street. I stared at the ceiling with my thighs still trembling and thought that what I had been putting off for so long had just happened, and that it hadn’t been perfect, but it had been much more beautiful, much dirtier, and much more intense than I’d imagined.

I didn’t have an orgasm that night. I came close, very close when he sucked my clitoris and when I rode him, but I didn’t quite get there. It would take me a few more months to learn exactly what my body needed to do to reach that point. But I remember perfectly that dawn, as I walked home with my hair still tousled and my cunt throbbing between my legs, still feeling the hollow where his cock had been. The only thing I could think about was that I wanted to do it again. Again and again. With him, with all the Andréses who might come along, with anyone. Something inside me had been unlocked that night, and I was still learning how to recognize it.